


A Good Time for a First Time

by CrashDevil (cjdevlin19)



Series: Crash Into Me [10]
Category: Supernatural
Genre: Angst, F/M, Fluff, Karaoke, Mentions of Eating Disorder, Smut, mechanical bull, mentions of self harm
Language: English
Status: Completed
Published: 2019-11-19
Updated: 2019-11-19
Packaged: 2021-02-13 11:46:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,792
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21493762
Author URL: https://archiveofourown.org/users/cjdevlin19/pseuds/CrashDevil
Summary: Dean takes a drive to clear his mind after Mary leaves.~~~~~~~~~“Wow,” he said on a breath when the door opened. She wasn’t dressed up, not like she was when he was in Florida last time, but she looked amazing. Dark blue jeans that hugged her curves, those black high-heeled boots that made her calves look so amazing, her hair was all that multichromatic blond color and she’d twisted it up with something that looked like a fancy chopstick. Her face was made up but it was simple colors: greens on her eyelids, wine red on her lips. The colorful shirt she was wearing caught his eyes, blue and red plaid flannel over a black camisole. “You look damn good in hunter colors, Crash.”“Thanks.” She looked down at herself, a bit self-consciously. “I always thought I couldn’t pull off plaid flannel without looking like a lesbian lumberjack, but I saw it at Maurice’s and it reminded me of you…Amanda swears it looks good.”“Amanda doesn’t lie. It looks awesome on you.”“Thanks,” she repeated, her cheeks going a bit pink.
Relationships: Dean Winchester/Original Female Character(s)
Series: Crash Into Me [10]
Series URL: https://archiveofourown.org/series/1341889
Comments: 5
Kudos: 13





	A Good Time for a First Time

**Story Warnings**: a bit of angst, so much fluff, so much smut **18+ HERE BE SEX DON’T READ IF YOU’RE A YOUNG’UN!!! **protected sex, oral sex (fem and male rec), fingering, little bit of pain kink, mentions of self-harm, mentions of eating disorder

_Wanna enhance your fanfic experience? Get Dean’s hydrosol from [@scentsfromthebunker](https://tmblr.co/mF5e4kRNNSBHQOyI0dZE0-Q)!!!_

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

It started as a drive. Just a simple “get out of the bunker and clear your head” drive. No real destination in mind had him taking turns indiscriminately and he ended up on the interstate heading South.

His mom needed time. Time, like she hadn’t had a fucking lifetime in Heaven! Time to deal with her grief, the loss of her sons that she was walking the fuck away from!

Of course, Sam was making him feel like he was overreacting. “Give it a bit. She’s just overwhelmed. Let her get used to the world and the idea of us. She’ll come around.”

So, Dean took a drive. When his anger got too big for the enclosed space of the bunker, he took Baby for a ride. He was six hours in, just passing Morris, Oklahoma, when he realized his turns hadn’t been so indiscriminate. He was heading Southeast toward Florida…and he was okay with that.

Getting back on track with Crash had been hard. She was so certain that he didn’t want her, that he _couldn’t _want her, that he had to constantly remind her.

He hated that her self-esteem was so low that she doubted every blatant sign in front of her. Hell, her best friend had told her, flat-out, that Dean wasn’t lying about the way he felt and Amanda was a damn Empath. Still, she doubted.

But she was coming around. She was getting more confident and with Amara gone, it was easier for Dean to spend his free time on the phone with her. Crash had called from the courthouse while he was on that haunting with Sam and their mom to tell him she’d finally filed for divorce. She was excited about it, happy to unburden herself from Mike.

Dean was going to celebrate with her. Maybe focusing on her happiness would force some in him.

He called halfway through Mississippi. “Hey, Crash! What’cha up to?”

“Nothing,” she answered with a heavy sigh.

“What do you mean ‘nothing’?” She was a mom with a job. She was never doing nothing.

“Well, I’ve been watching TV since I got home from work, but I count that as ‘nothing’.”

“Where’s your li’l rebel?”

“Atlanta. Mom and Dad went to rescue Jaimz from his mom the day before yesterday and they decided to take both of the kids to Legoland.”

Dean licked his lips. “Wasn’t yesterday your birthday?”

“Uh-huh, but I had to work so I couldn’t go to Legoland on such short notice. It’s fine. I’ve got the house to myself so it’s nice. I’m not wearing a bra or pants. Took ‘em both off as soon as I got home. Comfort without worry.”

“Awww. Well, I don’t want to ruin your comfort and you can definitely keep the bra off if you want, but you’re going to need to put on some pants soon.”

“Why?”

“Because I’m about three and a half hours away and we’re goin’ out tonight.”

He could hear her shift, likely sitting straight up on the leather sofa. “Really?”

“Really. 'less you don’t wanna.”

“Of course I do. I just wasn’t expecting it. Why do you always spring this shit on me?”

“I gave you more than three hours advance notice this time! That’s plenty of time to get ready!” Dean exclaimed. He was smiling already.

“Yeah, I know, but…fine. I’m gonna go shower and get ready. I’ll see you when you get here.”

“See ya soon, sweetheart,” Dean said, turning off his phone and turning up his _Physical Graffiti _cassette.

He stopped at a gas station just outside Walton, buying baby wipes and a cheap toothbrush and toothpaste. He freshened up in the dirty bathroom and changed his shirt before driving to Crash’s house. He parked in the driveway next to the motorcycles this time, instead of on the grass, and headed for the door.

“Wow,” he said on a breath when the door opened. She wasn’t dressed up, not like she was when he was in Florida last time, but she looked amazing. Dark blue jeans that hugged her curves, those black high-heeled boots that made her calves look so amazing, her hair was all that multichromatic blond color and she’d twisted it up with something that looked like a fancy chopstick. Her face was made up but it was simple colors: greens on her eyelids, wine red on her lips. The colorful shirt she was wearing caught his eyes, blue and red plaid flannel over a black camisole. “You look damn good in hunter colors, Crash.”

“Thanks.” She looked down at herself, a bit self-consciously. “I always thought I couldn’t pull off plaid flannel without looking like a lesbian lumberjack, but I saw it at Maurice’s and it reminded me of you…Amanda swears it looks good.”

“Amanda doesn’t lie. It looks awesome on you.”

“Thanks,” she repeated, her cheeks going a bit pink.

“So, where we going to celebrate your twenty-seventh birthday, kiddo?”

Crash scoffed. “I’m _older _so you’re back on the ‘kiddo’ business? How does that make sense?”

“Just didn’t want you to _feel _old,” Dean said, smirking. “Now, come on. Where we going?”

“We’re going to The Block,” she said, grabbing her purse from leather loveseat and slinging it over her shoulder.

“We’re going where?” Dean asked, securing the door behind her and following her to the Impala.

“It’s this place called The Block. It’s three clubs under one roof. Sports Block, Country Block and Cell Block,” she explained, pulling open the passenger side door and sliding in.

“Not really a ‘club’ kinda guy, Crash.”

“It’s less a club and more ‘three differently-themed bars smashed together in one building’. There’s a Sports slash Karaoke bar, a Country bar with a mechanical bull and the Cell Block is either new rock or rap music depending on the night.”

“If it sucks, I’m Googling the closest dive bar and we’re going there instead.”

“Sure!” she agreed, happily. “I mean, we’re celebrating _my _birthday, but fine. It’s fine.”

“It’s not just your birthday, sweetheart. Also celebrating your divorce.” Dean chuckled and turned the key in the ignition, turning down the music so she could give him directions to the club. He watched her walk carefully across the loose gravel parking lot, her hips swaying as she moved on those high boots. The bouncer let them in without asking for ID and Crash led him to the bar of the Karaoke club.

“You gonna sing somethin’?” he asked as they waited for the bartender to notice them.

“Totally! You?”

“Maybe. People didn’t seem too fond of my karaoke when I was-” Dean cut himself off and shook his head. “I’m not a good singer.”

“Bullshit! You just need a good song.”

“They booed me on Right Said Fred! Come on!”

Crash shook her head and laughed. “While I agree that you are, indeed, too sexy, Dean, no one actually _likes _that song. _You _don’t even like that song, do you?” He smirked as he shook his head. “We’ll find a good song, dude. I’ll even go up with you if you want.”

“Sounds good, sweetheart. Let’s get liquored up first.”

“Don’t gotta tell me twice,” she responded. She ordered them each a bourbon and handed the bartender her credit card to start a tab. “Oh! Come with me. You gotta meet Sugar!”

“Who the hell is Sugar?!” Dean yelled after her as she swiped her whiskey off the bar top and headed toward the Country Block.

“_That _is Sugar!” Crash called over the sound of a loud and upbeat Dierks Bentley song, pointing at a mechanical bull. Dean’s eyes lit up as he walked up to the edge of the foam safety mat. “You gonna ride, cowboy?”

“Are you?” he asked, eyebrows raised high. She just smiled in response. “Seriously, can you handle that thing?”

“Ye of little faith. Hold my drink… and my purse.” She shook her head and offered both to him. He scoffed and took the purse by its strap and the bourbon by the edge of the cup. She bounced over to the DJ booth in the corner. He noticed her point to him, but he just licked his lips and leaned against the enclosure as Crash climbed over into the pen.

As soon as the song ended, the DJ picked up a microphone. “All right, Country Block, we’ve got a treat. Someone has decided to brave Sugar! Give Cassie a big hand!”

Dean watched from the sidelines as an attendant helped Crash up onto the bull and she wrapped her right hand around the rope. A new song started as the machine started to buck under her. She moved her body to compensate, rolling her hips and gyrating against the saddle, leaning back or forward depending. It was obvious that the bull’s controls weren’t set very high, but also that she’d been on Sugar before. Dean’s cock twitched with interest at the thought of her riding him like that.

She made it halfway through the song before a particularly sharp twist had her losing her grip and flying off to bounce off of the mat. He could hear her laughter from across the bar, over the sound of the music and the sounds of the other patrons, and he heard a distinct ‘woot!’ as the attendant helped her up.

She rushed over to Dean and climbed over the enclosure, smiling up at him as she took her whiskey and purse back from him. “Minute thirty-eight! My previous best was a minute seventeen. Gettin’ better.”

“How often do you ride that thing?”

“Oh, I’ve only been on it, like, four times in the last eight years. First time I only lasted twenty-three seconds. So, you gonna give it a try?”

“Are you kidding me?” Dean smirked. “I _have _to try it.”

“Good. I told the DJ to run Sugar on expert for you,” Crash said, taking a drink of her whiskey and gesturing at the enclosure. He chuckled and climbed into the pen.

Dean wrapped his hand in the rope and lifted his left into the air. He winked at Crash as the bull started to move under him and she grinned stupid big, leaning against the enclosure and sipping at her whiskey. As she watched him roll his hips and compensate for Sugar’s movements, her eyes went dark and her jaw hung slack. He could tell her mind had gone to the same sexual place his had.

As Sugar bucked under him and he held on with his thighs, Dean knew how the night was going to end. He was finally going to get her naked, finally going to show her exactly how much he wanted her. He was going to make her scream.

He went flying off of the bull, his wandering mind making it impossible to concentrate on the task before him. “Seventy-four seconds,” the attendant informed, as they helped him up. “Not bad for a first-timer.”

“What can I say? I shoulda been a cowboy.” Dean smirked as he climbed out of the enclosure next to Crash. “You enjoy the show?”

“Immensely.” She chuckled and headed for the Karaoke bar. “Your thighs are gonna hate you tomorrow.”

“I believe that.” Dean followed her to a small square table with a thick white binder on it. “So, what’cha gonna sing?”

“I usually start with ‘Gunpowder and Lead’, then go to ‘Hotel California’, ‘Magic Man’ if they have the version without the thirty-two bar break in the middle and then…it depends how drunk I am by that point. Sometimes I’ll go into Taylor Swift territory, sometimes I’ll go Anna Nalick’s ‘2 AM’. If I’m feeling especially brave-drunk, I’ll do ‘Cherry Bomb’ or ‘Bad Reputation’.”

He chuckled as she started to write her choices on little slips of white paper. “So you don’t need this book at all, do you?”

“I mean, depends how many songs we can do. And if you wanna do a duet with me or not.”

“Maybe.” Dean licked his lips and leaned forward. “You got anything in mind?”

“Maybe,” she responded, looking up from her work. “How do you feel about Meat Loaf?”

“It’s delicious.” He laughed at the bitch face she presented him with. “You mean Michael Aday?”

She smiled. “I assume since you called him something other than Meat Loaf or Bitch Tits that you’re not a hater?”

“His name was Robert Paulson.” Dean smiled and shrugged. “I’m all right with him. Don’t tell Sam. That’s like admitting I’m okay with Bon Jovi.”

“You _are _okay with Bon Jovi,” she said, smiling. “I’ve heard you humming 'Dead or Alive’ on the phone before.”

“Don’t tell Sam,” he repeated, smirking.

Cassie hummed and nodded. “Anyway, Meat Loaf has two really good duets that are almost impossible to fuck up no matter how bad you think you sing and they both have the added bonus of the hard-driving difficult parts being the female parts.”

“Oh, really?”

“Uh-huh. Example. _'I would do anything for love, I’d run right into hell and back. I would do anything for love but I won’t do that’,_” she sang quietly, then took a deep breath. “Versus ’_Will you hold me sacred, will you hold me tight? Will you colorize my life, I’m so sick of black and white?_’ See?”

Dean nodded. The female part definitely had more power behind it. “You’re not wrong. So you’ll carry me through a Meat Loaf song?”

She licked her lips and nodded. “Gladly.”

She took up the slips to the karaoke DJ as Dean got them both another round of whiskey. They sat and talked about everything and nothing as they waited for her name to come up on the screen. Mary returning was a major interest to Crash, who immediately launched into the psychological impact of coming back after more than three decades. “The world is a completely different place! _You’re _completely different. I mean, I don’t endorse her leaving because how is she gonna get to know the men you became if she’s off doing whatever, but I understand her being overwhelmed.“

"Oh, I understand her being overwhelmed! But we can’t help her acclimate now!”

“I don’t think she needs you to help her acclimate, Dean. She’s a hunter. Improvisation and bullshitting your way through life are kinda main traits. I’m more upset for you that she didn’t want to get to know you, ya know? 'Cause you’re fucking awesome.”

Dean smiled softly as Crash got called up to sing. She had an apprehension on her face as she walked away from the table and took her place on the stage. He’d heard her sing before, but he had never seen her _perform_. As the music started, her legs were shaking, but she hid it by tapping her toe to the beat of 'Gunpowder and Lead’.

As she belted out the first verse, the fear seemed to melt off of her. She didn’t need the words on the screen, it was obvious she knew the song by heart. By the time she got to ’_his fist is big but my gun’s bigger_’, she was bouncing on her boots.

“Damn, baby, that voice is golden,” Dean said, as she found her way back to the table. Even in the dim light of the bar, Dean could see her cheeks burn bright. He smiled, loving making her blush. “Baby, I’m so glad you’re my duet partner.” Her cheeks went darker. It was amazing how a word like ‘baby’ could make her melt.

So of course Dean had to pepper the word through the conversation. “You’re doing it on purpose,” she complained, putting her beer bottle to her cheek.

He smirked, his tongue poking just slightly between his teeth. “What gave it away, baby?”

“That!” she groaned. Dean just chuckled. She was a lot of fun.

She got up and sang several times, slaying The Eagles and Heart before moving to a Sylvia song. He grew more impressed as the night went on and the alcohol and adrenaline showed her true personality. That bad-ass switch he saw get flipped the first day they met. When “I’d Do Anything for Love” came up with both of their names on the screen, she grabbed his hand and pulled him toward the stage.

As he sang, giving no care about his pitch, Crash provided harmony no matter what his voice was doing. Dean kept his arm wrapped around her shoulder, her body pulled against his side. When it came to her part, he released her so he could turn to her and watch her kill her lines.

“_Will you raise me up? Will you help me down? Will you get me right out of this Godforsaken town? Will you make it all a little less cold?_” Dean responded with ‘I can do that, I can do that’, thinking, not for the first time, about stealing her away from Walton. “_Will you hold me sacred? Will you hold me tight? Will you colorize my life? I’m so sick of black and white! Can you make it all a little less old?_” ‘I can do that. Oh, oh, now, I can do that’, he responded, but it could barely be called singing. She took a deep breath and he could tell that she was about to flip that switch. “_Will you make me some magic with your own two hands? Can you build an emerald city with these grains of sand? Can you give me somethin’ I can take home?_”

Dean forgot his line, engrossed in watching her green eyes sparkling as she sang. She was looking at him, too. Begging him to give her something real, something worth a damn. “_Will you cater to every fantasy I’ve got? Will you hose me down with holy water If I get too hot? Will you take me places I’d never go?_”

“Oh, I can do that,” Dean whispered before snapping out of it and raising his microphone again. “Oh, oh, now, I can do that!”

Her eyes went a bit sad as she went on to the next verse. “_After a while you’ll forget everything. Just a brief interlude and a midsummer night’s fling. And you’ll see that it’s time to move on._”

“I won’t do that,” Dean assured her. “I won’t do that.”

“_I know the territory. I’ve been around. It’ll all turn to dust and we’ll all fall down. Sooner or later you’ll be screwin’ around._”

They finished out the song and headed away from the stage. “We won’t turn to dust, ya know?” he said, when they got back to the table and he pulled her into his lap. “Saw how your eyes went weird at that part.”

She blushed and tried to move off of his lap, but he put his left hand on her thigh. She gasped and he barely heard it over the sound of the Luke Bryan wannabe on the stage. “Dean, I-”

“You got nothing to worry about, baby. I’m not gonna screw around.”

“You gotta stop callin’ me that, Dean,” she said, quietly.

“Why, baby?” he responded with a smirk. “Thought you liked it.”

Her lips pressed into his immediately and his hand tightened around her thigh, making her whine into his mouth. Their tongues slipped against each other and Dean’s cock started to swell in his pants as Crash grabbed at his shoulders and neck. “Take me home, Winchester,” she whispered, slipping off of his lap and grabbing her purse off of the table.

“What about your last song?” he asked, but he was already pulling his keys from his pocket as he stood.

“I’ll give you a private performance on the way home. A little Joan Jett?”

“‘Bad Reputation’?” he asked as they walked toward the parking lot.

She turned to him with a flirty smile. “_Every girl an’ boy Needs a little joy All you do is sit an’ stare. Beggin’ on my knees Baby won’t you please Run your fingers through my hair._” Dean chuckled as she started dancing backward toward the Impala. “_My my my Whiskey and Rye. Don’t it make you feel so fine? Right or wrong Don’t it turn you on? Can’t you see we’re wastin’ time, yeah._”

Dean surged forward, pressing her against the hood of his car with his body. “Yeah, I wanna touch you, Crash.” He groped at her hips, grinding his erection into her thigh. She whimpered as he kissed her neck. “Wanna taste you. Wanna fuck you,” he whispered in her ear.

“Oh!” she gasped out a breath. “D-Dean.”

“You’re gonna be screamin’ that soon.”

“Not-not in the parking lot,” she insisted.

He laughed against her skin. “Ruin my fun.” He pulled back and she slid off the hood onto wobbly legs.

“I have to live in this town, Winchester. I don’t want to have to deal with an Indecent Exposure charge or something. Take me home and we can be as indecent as we want.”

Dean helped her in the passenger side and she smiled at him through the window as the door creaked shut. He wasn’t five minutes into the drive to her house when she slid across the bench and started pressing kisses to his jawline and behind his ear, her hands lightly massaging his right thigh. “Uh, what’cha doin’, sweetheart?”

“Nothin’,” she responded, coyly.

“I’m trying to drive, Crash,” Dean protested weakly as her right hand moved to cup him through his jeans.

“I’m sure you can drive just fine, hero. See, I’ve been wondering how big this thing is for fuckin’ _years_. I knew it was big from when you were trying to teach me how to shoot pool, pressed up against my back, but I have been wondering just _how_ big. Trying to figure out if I could even fit it in my mouth, how it might stretch my pussy, how-”

He groaned, his fingers tightening their grip on the steering wheel. “Holy shit! You’ve got a dirty fuckin’ mouth, don’t you?”

She laughed and licked his neck. “I write erotica, Dean. Dirty mouth, dirty mind, dirty intentions.”

He licked his lips and tried to focus on the road as she started to work the buckle of his belt. “What, you can’t wait ‘til we get you home to-”

“I just wanna know if it’s as big as I think it is.”

“How big do you think it is?” he asked as his belt hung slack and her hands went to the brass button.

“Bigger than anything I’ve had in me in at least seven years,” she responded with absolute confidence.

“Oh?” He almost squeaked as she reached in the open front of his jeans and wrapped her fingers around him. “Mike’s not-”

“Four and a half inches. No girth. Think Expo marker and you’re in the right ballpark.“ She hummed, appreciatively as she ran her fingertips along the velvety skin of his erection. “He’s the smallest I’ve ever had, actually.”

“And seven years ago?” Dean asked, shifting his ass forward to give her better access.

“A threesome with one of Mike’s friends back when we were still just dating… well, we were engaged.”

“And Mike’s friend was-”

“Gifted…to say the least.”

“Not one of those pricks I met in Alabama?”

“No, not Chris or Will. The one who had better things to do, Joey. He went into the Army, got some _real _survivalist training.” She hummed and pulled him out of his boxers, gasping when she finally got to see it. She swallowed thickly, as she closed her fist around him and slowly ran it up and down as much as she could with his pants and boxers in the way. “Wow.”

“What?” He shifted again, trying to get his pants out of the way.

“It’s just…been a while.”

"Since?”

“Since I saw a dick I really _wanted _to suck.” Dean groaned at her words and the way her fingers somehow knew exactly the right amount of pressure. “See, I used to have this unwavering love of oral. But Mike ruined that, as he does all things. I’m not even sure if I’m still any good at it, anymore.”

**__________SMUT STARTS HERE_____________**

She said the words with amusement, but there was a hint of real worry behind them. “Sweetheart, if you’re as good with your mouth as you are with your hand, you got nothing to worry about.” She leaned down, opening her mouth and giving the head of his cock a kitten lick. Dean let out a sharp breath, his fingers tightening on the steering wheel. “Shit, are you really doing this right now?”

“Do you want me to stop?” she asked as she flattened her tongue and licked at the vein along the side of his dick.

“_Fuck_! Nope. No, I do not want that.” She smiled as she wrapped her lips around his swollen cockhead. Dean was warring within himself as she started to take him further into her mouth, sucking lightly and caressing the underside of him with her tongue. Part of him wanted to slow down, not wanting to leave the hot, wet suction of her mouth like he knew he’d have to when they got back to her place. The other part wanted to speed up, get to her house as fast as possible so that he could get between her thighs and return the favor.

His right hand dropped to the back of her head as she took him in deep enough to gag herself. “Fuck, Crash.” She pulled back, sucking hard until she got to the head, where she swirled her tongue. “You’re really good at that.”

She pulled off of him with a soft pop and sat up, smirking happily with her swollen lips. “Haven’t lost my touch, after all.”

“No, you haven’t,” Dean muttered as he tucked himself back into his boxers. “So, how’d Mike-”

Cassie shook her head. “It’s complicated emotional abuse stuff that I blocked out for years. Can we leave it for tonight? I wanna enjoy being with you for right now, okay?”

Dean nodded, pressing his foot on the pedal harder to get them to their destination. She pushed her way out of the car as soon as he put it in park and pulled her keys, unlocking the door and rushing for the stairs before stopping to take her boots off. Dean kicked the door closed and moved to pull his boots free of his feet, too. He met her on the stairs, pulling her into a kiss and grabbing at her flannel to push it down her arms. “Bedroom,” he demanded softly into her mouth as the blue and red plaid dropped to the stair she was standing on.

“Okay,” she said on a breath, turning and taking two steps at a time to get to the landing at the top of the staircase. She opened the first door visible from the landing and walked in, peeling her camisole off over her head. Dean smiled at her bedroom. Lime green walls, covered in posters from her favorite bands and movies and a cutout of Hawkeye from the Avengers comics that obviously used to be part of the packaging for some toy. She obviously kept the bed in the divorce, a large king-size mattress up on a metal frame with no back or footboard. There were clothes on the floor but Dean didn’t care. He pulled his jacket and flannel off and threw them on the floor, too.

Crash dropped her jeans and stepped out of them, flopping onto the bed and smiling nervously across her bedroom as he pulled his shirt off. Her arms were crossed over her belly, seemingly trying to hide it from him. He licked his lips and stepped up in front of her, smiling down as she looked up into his eyes. “You can’t get bashful now, baby. You’ve already had my cock in your mouth.”

“I haven’t done this in a while, D. The ‘first time’ thing,” she whispered, green eyes sparkling with worry. “Sex, at all, really. _Good _sex even longer. Oral…blowjobs are easy, they’re default. But…what if-”

Dean smiled softly and reached out to cup her cheeks, swiping his thumbs across her skin. “Crash, you’re amazing. You’re brilliant and sexy and I have wanted to see what you look like naked since you walked out of _Elements _and hopped on that motorcycle. The way your hips moved when you were changing lanes on that thing? A lot like watching you on Sugar tonight. You can _move_, sweetheart. Let’s move together, huh?”

“Gods, you’re a corn-ball.” She chuckled and reached up to cover his hands with her own. “I love it.”

He smirked and leaned down to press a kiss to her lips. “Good. Now, take off your bra.”

She reached behind her and unclipped her bra, tossing it across the room where it landed on the TV stand he recognized from the living room at the apartment. Dean groaned at the sight of her breasts, large and natural with pink nipples hardening quick in the cold of her bedroom. He pressed her back to lie on the bed, letting his large hands cover her tits before sliding down to her hips. She gasped as he joined her on the bed, immediately attaching his mouth to her nipple. “Oh! Fuck, Dean. Oh, gods!” she gasped out, quietly.

He smiled against her breast, flicking his tongue across the hard nub, marveling at her hypersensitivity. Of course, he was good and she was deprived, so she really didn’t stand much of a chance. He started to kiss his way down her body, left hand kneading her right breast as he started to tongue at her soaked panties. Her hands twisted in the sheet under her as he pulled her panties to the side and started to lick slow deliberate stripes across her most sensitive parts. He slipped his middle finger into her and started to pump it in and out, curling it on every sweep to keep her gasping. But not moaning.

“Come on, baby, I know you can be louder than that.” He looked up at her from between her thighs, still sliding that finger in and out of her wetness. “Your family’s gone, Crash. Be loud.”

“What? This _is _loud.”

Dean’s eyebrows shot up. “I’m sorry, what? Over here with your church mouse impression, you think you’re being loud?” Her face turned dark pink with her blush and she covered as much of it as she could with her palms. Realization hit him and he scowled. “Mike didn’t like you moaning, huh?”

“I’m sorry,” she squeaked.

“You got nothin’ to be sorry about ‘cept maybe marrying that piece of shit. He trained you to be quiet, I’m just gonna have to break that training and instill my own.” Her pussy clenched around his finger at the mention of ‘training’ and he smiled, putting away the kink knowledge for later use. They needed to have some semi-vanilla sex before they jumped into whips and chains. “Gonna teach you how to scream,” he promised, adding a second finger and pumping them harder.

“Oh!” She licked her lips and closed her eyes, visibly trying to relax enough to let her moans out. He went back to work with his mouth, lips and tongue working across her clit and the surrounding skin as he fucked her with his fingers. Her left hand curled into the sheet again but her right went to his hair, tugging insistently as she got closer to climax. “Oh, fuck, _Dean_,” she whined.

_***Gettin’ louder***_ he thought triumphantly as her pussy walls started to flutter. He crooked his fingertips to seek out her g-spot and smirked when she let out a deep, loud moan. _***Good girl!***_

“I’m so close. So fuck- oh, god. Dean, fuck, just-” she babbled as he continued his work. When her orgasm finally crashed over her, she went stiff, her eyes rolling back as she let out a guttural noise that made him proud. Dean pulled away, leaning back to watch her come down from her high. She really was gorgeous; her chest was heaving, her face completely flushed, bliss written across every feature. “That was really good. Holy shit!”

“Don’t know if you noticed, but you actually moaned there a few times,” he teased, stretching out beside her and reach out to play with her nipple, rolling it and pinching lightly.

She shifted onto her side and grabbed at the back of his head, licking into his mouth. “Least I taste good,” she whispered, and he moaned, his cock twitching in his pants like it was trying to get harder…which wasn’t even remotely possible.

“Fuck. I forgot you like pussy, too.”

“Take your pants off, D. I want you in my mouth again.”

“Don’t gotta tell me twice,” he muttered, popping the button and pulling the zipper down before tearing the denim down his legs, cotton going with it. He licked his bottom lip between his teeth and she wrapped her hand around the base of his uncomfortably hard and throbbing cock and leaned down to take him in her mouth again.

With his clothes out of the way, she was able to reach her left hand out and gently massage his balls, right hand jacking what she couldn’t get in her mouth with slight twists of her wrist. Both of Dean’s hands came down to fist in her hair, not forcing a change in her rhythm, but definitely holding on for dear life. She was way too good at that. He was not gonna last. He yanked at her hair, a little harder than he intended in his haste, and she let out a wanton moan as he pulled her away from him.

_***Another piece of kink to file away for later use,***_ he thought, wrapping his arm around her and hauling her back up the bed to roll on top of her. “Sorry. Not as young as I used to be. If I blow my load now, I’ll need time to get going again.”

She nodded, licking at her swollen lips. “Okay.”

“You got condoms? I got-”

“I’m allergic to latex,” she interrupted, twisting under him to point at a small gold-colored metal box sitting on an ottoman at the foot of the bed. “There’s poly condoms in the toy box. Code on the lock is 616.”

“‘Toy box’?” Dean questioned as he rolled toward the end of the bed. The golden box with the small steel lock on the clasp had a scantily-clad blond elf on it, shackles attached to her wrists, the word ‘Everquest’ emblazoned across the bottom.

“Don’t judge the box, Dean, just get it open already.”

“Okay, but what the fuck is-” he asked as he pulled the box to the bed and started to slide the numbers on the lock.

“It’s a game I used to play with my dad. It’s like World of Warcraft before WoW was a thing.”

“And you keep your sex toys and condoms in the box because-”

“Because I have a nosy child who I don’t want touching those things, I don’t have much in the way of toys, Mike wouldn’t let me buy anything bigger than him so most of my toys are small, and that box fits the little luggage lock I found when I was cleaning to move into the apartment and because I’m a fucking geek and you knew that already so open the box and let’s fucking do this!”

Dean raised an eyebrow as he pulled the lock open and flicked the lid open. Several small vibrating dildos sat in the box with a small egg-shaped vibe and a box of Trojan condoms, but Dean ignored all those in favor of the purple rubber instrument shoved in the bottom of the box with a set of handcuffs. The flogger was obviously not made to do real damage, just a sting of pain to enhance the pleasure. He held it up, smirking. “At least your ex indulged your kinks a bit.”

Crash snorted. “No one’s used that on me since high school.”

Dean rolled his eyes and let the flogger fly, the tails landing against her breasts and making her gasp sharply, followed by a low moan. “We’ll play with this pain thing you got later. Right now-”

“Please, get a damn condom on,” she begged.

Dean just smiled and grabbed the Trojan box, shaking a few out onto the bed and tossing the box back into the toy box with the flogger. He rolled the condom on with ease, making certain it was secure before he laid himself out over her body. Her legs came up to notch at his hips as Dean started to kiss her, his tongue moving against hers. Her hands went to his shoulders as they made out, taking their time before moving to the next stage; the official transition from friends to lovers.

“You ready, baby?” he whispered, moving to take her earlobe between his lips. She nodded, slightly, and he pulled back to look into her eyes. “Can’t wait to feel you, Cassie.”

Her eyes widened just slightly at the use of her name and they blew out big as he reached between them and guided himself into her entrance. Her hands tightened their grip on his shoulders as he started to rock into her, getting a little further with each motion. He loved watching the overwhelmed expression on her face, the way her eyes rolled when he finally got all of his cock into her. “Holy fuck,” she whispered.

“You’re fuckin’ tight as fuck, baby,” he whispered back, licking at her collarbone as he gave them both a moment to adjust.

“I mean, everybody’s gotta be tight with how big you are,” she responded.

“Yeah, true, but you’re not the first MILF I’ve had…but somehow, you’re still-”

“Aria was a c-section…and I’ve been doing kegels my whole life.” She clenched her muscles to illustrate her point and he hissed, his eyes closing in response. “Sorry.”

Dean buried his hand in her hair and kissed her fiercely as he started to move his hips, thrusting hard into her, pushing the air from her lungs on every pump. His left hand dropped to her thigh, rough fingertips groping her flesh with bruising pressure. He pushed her knee up toward her chest, smiling against her lips as her other leg mirrored the movement and the angle changed.

He grabbed her ankles and put her feet on his shoulders, leaning back to watch as his cock slicked in and out of her. “Fuck, that’s pretty.”

“Oh, God, D.,” she panted out, grabbing at his arms. He leaned forward, speeding up again as her whining moans got louder.

“There ya go, baby. Louder for me, sweetheart.”

“_Fuck_! Dean, fuck, please!” Her nails dug into his forearms but he didn’t care, fucking into her harder to get those noises, that strung-out look on her face, the desperate panting, the clenching of her muscles around his cock.

“You ‘bout to cum again?”

“Yes, yes, shit, yuh…” She reached down to rub at her clit, but he grabbed her hand and tossed it away, pulling out abruptly and removing himself from her body. She looked up at him, at a complete loss.

“Not yet, sweetheart. Hands and knees,” he demanded, slapping his hand against her inner thigh.

“Oh! You asshole.”

Dean chuckled, smirking down at her as she sat up glaring at him. “Look, we’ve both been waiting for this for years. You want it to be done already, or do you want to know what it feels like to get fucked thoroughly by someone who actually knows what they’re doing?” Her mouth dropped open and she gave a little sigh before flipping over and raising to her hands and knees. “That’s what I thought.” He reached out and slapped his hand across her right asscheek, smiling as her whole body jerked. “I love your ass.”

“Well, glad one of us does.”

“Shut up, your ass is amazing,” he said, slipping his thumb down the crack of her ass to rub at her asshole.

“Oh! No, no, no! I don’t do butt stuff.”

He pulled his hand away and let it slide across her lower back. “Have you _tried _it?” he asked, gripping his cock with his other hand and guiding the tip back into her pussy.

“Y-yeah. It just hurts and n-not in a good way.”

“Tried it with Mike or one of the bigger-” Dean cut himself off with a hiss as she pressed back into him, impaling herself on his cock.

“The other three were all one night stands. They didn’t even ask.”

Dean jerked his hips forward and she cried out. “Then Mike fucked it up.” He leaned over her, reached around her body to grab her hanging breasts. “Maybe on our second night I’ll show you how that’s supposed to feel.”

“Oh,” she said, gasping as he started to pinch and pull at her nipples. “Mayb-be.”

“Good girl,” he whispered before beginning to piston his hips, his cock slamming back into her over and over.

He decided her pleasure sounds were one of the best things about fucking her. Not just because it was a challenge to get her to make those noises, but because they were so fucking pure. These weren’t the porn star noises he’d heard from roadhouse chicks trying to put on a show. These were honest, uncontrollable, and _he _was pulling them from her.

Her arms started to get tired. It actually took longer than he expected for her elbows to start shaking. “Drop to your elbows, sweetheart. Just keep your ass up.” She did what he said immediately, letting out a sigh of relief as he gave her a minute to get resituated before he started to fuck her again. Her moans were muffled by her blanket but that just seemed to spur her on. He was certain she was babbling his name into the brown cotton but he couldn’t tell. “God, you feel so fuckin’ good, Crash. So soft and warm and perfect. Such a perfect pussy, baby.”

She screamed into the fabric, fucking back into his every thrust as he praised her. She turned her head to the right and took several panting breaths. “So close, Dean. Fuck, please. I-”

“Yeah, me too, baby. Play with your clit, Crash. Wanna feel you cum on my cock.”

“Oh, my gods!” she whined, holding herself up on her left elbow as she shoved her right hand beneath her to rub her fingertips across her clit. She was quiet when she came the second time, her mouth open in a silent shout as her body went stiff and her pussy clenched tight around his cock. Her internal muscles fluttered hard around him and he only lasted three more thrusts into her heat before he was shooting his load into the condom, grunting low in his chest.

**_______SMUT ENDS HERE_______**

“Wow,” he whispered as he pulled out and stumbled backward off of her bed. He slipped the condom off and walked over to the trashcan next to her bedroom door. By the time he turned back to the bed, she was on her back with her head on the pillow. He gave her a dopey grin as he walked back to the bed. “Why the hell did we wait so long?”

“I was married? You were cursed? It wasn’t a good time ‘til tonight?” He flipped over her, landing on what used to be Mike’s side of the bed and pulling her into his arms. “Ooh, show off!” she accused, with a smile.

“I’ve been showing off all night, why stop now?” She laid her head on his chest and grabbed the comforter to cover them both. “So, when’s the rest of the family get back from Legoland?”

“Wondering if you need to disappear or wondering if you need to wear clothes when you wake up?” she asked, amusement in her tone.

“Yes,” he answered without specifying.

She chuckled and looked up at him. “Tomorrow afternoon. So we can be naked together for a few hours before we-”

“Good,” Dean interrupted, not wanting to think about leaving yet. “I’m much happier in the buff.”

“I’m much happier with you in the buff, too, D.,” she said, smiling.

Dean pulled her hair out of her face and leaned his head down to press his lips to her forehead. “Pancakes in the morning?”

“Yeah, we got some pancake mix down in the pantry. I’ll make-”

“_We’ll _make breakfast. I _can _cook, ya know.”

She smiled and nuzzled her head into his chest. “Thank you for coming to celebrate my birthday-divorce with me.”

Dean hummed in agreement and settled into the mattress. “You should get a memory foam mattress,” he suggested, letting his eyes drift closed. “_My _mattress remembers me.”

“I’m sure it has a million stories to tell.”

“Oh, no. No, that mattress only has three stories. Porn, Pizza, and Poor Sleep Habits.” He sighed, exhaustion taking over him. “I don’t have women at the bunker. Kinda defeats the purpose of a secret, underground batcave if…women know…women know about it.”

“No wonder I’ve never gotten an invitation.”

“I’ll show you…around someday. You’re not just any woman,” he mumbled. They both fell asleep with tired smiles on the faces.

~~~~~~~~~~~~~~

Waking up next to a warm body was nothing new for Dean, but waking up next to someone he had absolutely no desire to leave was something he hadn’t felt since Lisa. And even then, he did kinda want to leave. Much as he loved playing house with Lisa and Ben, he’d missed Sam too much to fully immerse himself in the apple pie life.

He let himself watch Crash sleep for a few long moments, the rise and fall of her breathing, the softness of her facial expression, how her nose crinkled when her ceiling fan blew her hair across it. He started to count her freckles. He knew she had a galaxy of them across her cheeks and nose but now that she was naked beside him, Dean could see her shoulders and back were speckled with them, too. He was rounding seventy-eight when he noticed the scars on her arm. Most of them were faint, thin, old, but he still didn’t know how he’d missed them for so many years.

He moved the blanket slowly off of her so that he could see the expanse of her skin. Her outer thighs were littered with thick white lines and there were several across her stomach. **_*How’d I miss the ones on her tits? She’s got almost as many scars as I do.*_**

She stirred under his gaze, eyes fluttering open. “Good morning,” she groaned, stretching out her arms and legs.

“Mornin’.”

“What?” she asked, her eyes suddenly sleepless and alert when she saw his face.

“Just comparing scars. Knife wounds? Well, those are a lot neater than bullet wounds.” He said the words softly, conveying his desire to understand in his tone.

“Oh.” She looked down and licked her lips, sitting up. “Razor blades, actually. I-I used to be a cutter.”

“Used to be?”

“Haven’t cut myself since you were a demon, Winchester. I don’t-” Dean closed his eyes as guilt flooded him. “I didn’t even cut when Mike left me. I want to be able to tell Aria it’s all in the past when _she _notices my scars.”

“Crash, I’m so sorry.”

“It’s not a big deal. I don’t do it anymore. Most of these are from back in high school, anyway.” She slid off of her bed and walked to the closet, pulling panties from a Rubbermaid box on the floor and grabbing a blue sundress from a hanger.

“And which ones are from what I said to you when I was a demon?” he asked, dropping his legs over the side of the bed and watching her get dressed.

She hesitated, busying herself with the straps of the dress. “I don’t remember.”

“Don’t lie to me, Crash.”

“It’s not important, Dean. It wasn’t…I should never have…” She turned to look at him but he was just staring at her, resolute that she tell him. She sighed and hiked her dress up to reveal her thigh. She pointed to a thick scar about two and a half inches long before pointing to another just above her knee. The second was thinner but longer. “These two. I also drank a lot and shoved my fingers down my throat because you called me fat. Why does that matter now?”

Dean’s jaw twitched as he looked from her pale skin to her bright green eyes. “I thought what I said didn’t affect you that much. Thought you were made of stronger stuff.”

“I lied,” she said, succinctly, dropping her dress to cover her thighs again. “You believed me, so really, whose fault is that?”

Dean shook his head. He hadn’t believed her. He just didn’t think it was so bad. “I shouldn’t have believed you. I should’ve called you out on it.”

She sighed and walked in front of him. “It was, like, years ago. It doesn’t matter. I’m not upset anymore, you aren’t a demon anymore. You don’t really think any of that, right?”

“Of course not.” He reached out to take her hands and smiled, sadly. “I know it was two years ago, but I hurt you, sweetheart. I hurt you and you have literal scars from it. I’m so sorry.”

She leaned forward and slotted her lips against his. “None of it matters,” she whispered. “Last night was healing in ways you can’t even imagine, Dean. I had fun and I felt comfortable in my skin, scars and fat and all of it. I’m trying not to dwell on the pain of the past.”

He dropped her hands and grabbed her head to pull her into a deep kiss. “You’re amazing, you know that?”

She smiled and nodded. “Not as amazing as you.” She kissed him again and stepped back. “You gonna make me some pancakes now?”

“Thought _we _were making breakfast?”

“Yeah. You make the pancakes, I’ll make the eggs and bacon.”

He smirked. “Well, if there’s gonna be bacon, I should probably put pants on. Wouldn’t want grease poppin’ on anything important.”

Crash laughed. “Damn, I was really hoping you’d walk around naked all day.”

“Well, I was gonna, but then you said 'bacon’ and I ain’t riskin’ the goods.” Dean stood and walked over to grab his boxers and jeans off of the floor.

“I could cook sausage instead if you-”

“Woman, you said 'bacon’!”

She laughed, loud and unrestrained. “Okay, okay. Bacon, it is.”

They moved around the kitchen together, loving touches almost second nature, stolen kisses in moments of waiting for the food to be flipped. They ate and talked and laughed over their coffee mugs.

“You’ve got more freckles than me,” he said as she walked him to his car later.

“I wasn’t counting last night, Dean. I had my face in the mattress for half the event.”

“But you enjoyed havin’ your face in the mattress. That angle is somethin’ special.”

“You’re trying to make me blush,” she accused.

“I don’t gotta try, baby.” He smirked as she turned pink. “See?”

“Oh, shut up,” she demanded, her cheeks darkening further.

Dean cupped her cheek and leaned down to bump his nose against hers. “I had a great time last night, Crash. I can’t wait for next time.”

“Well…we don’t…” she hesitated, her eyes casting downward. “We don’t see each other very often so…”

Dean smiled. “This doesn’t make us a _thing _if you don’t want. You’re one of my best friends and I don’t want you holding out for me when I’m only around for a few hours every year or so. Just don’t tell me about it unless you get serious with someone. Deal?”

She nodded, looking into his eyes again. “Deal. Same goes for you. I know you have needs. Don’t hold back from the pretty waitresses and slutty roadhouse girls on my account.”

“Sounds good. I’ll call you when I get back to the bunker, huh?”

Crash nodded. “Please.”

Dean sealed his lips over hers and didn’t pull away until they needed to breathe. “See ya, sweetheart.”

“See ya, Dean.”


End file.
